Polyfunctional oxetane-based compound and production method thereof

Abstract

A group of polyfunctional oxetane-based compounds having a structure as represented by general formula (I) or a product obtained by a reaction between a compound of general formula (I) and epichlorohydrin, an ester compound, or an isocyanate compound. When these polyfunctional oxetane-based compounds are used as cation polymerizable monomers in combination with an epoxy compound, the curing speed is high, and the cured product has highly excellent hardness, flexibility, adherence, and heat resistance.

What is claimed is: 
     
       1. A cation polymerizable monomer generated by a reaction of a polyfunctional oxetane-based compound and epichlorohydrin,
 wherein the polyfunctional oxetane-based compound has a structure represented by formula (I): 
 
       
         
           
           
               
               
           
         
         wherein, 
         R 1  represents a C 1 -C 40  linear m-valent alkyl group, a C 1 -C 40  branched m-valent alkyl group, a C 2 -C 20  m-valent alkenyl group, or a C 6 -C 40  m-valent aryl group, wherein —CH 2 — can be substituted with an oxygen atom, —NH—, or 
       
       
         
           
           
               
               
           
         
       
       provided that two —O-'s are not directly connected, and wherein one or more hydrogen atoms in these groups can be each independently substituted with an alkyl group, a halogen, or a nitro group,
 R 2  represents a C 1 -C 20  linear alkylene group or a C 1 -C 20  branched alkylene group, wherein —CH 2 — in the main chain can be substituted with an oxygen atom, provided that two —O-'s are not directly connected, and wherein one or more hydrogen atoms in the group can be each independently substituted with an alkyl group, a halogen, or a nitro group, 
 R 3  represents hydrogen, a halogen, a nitro group, a C 1 -C 20  linear alkyl group, a C 1 -C 20  branched alkyl group, a C 3 -C 20  cycloalkyl group, a C 4 -C 20  cycloalkylalkyl group, a C 4 -C 20  alkylcycloalkyl group, a C 2 -C 10  alkenyl group, or a C 6 -C 20  aryl group, wherein one or more hydrogen atoms in these groups can be each independently substituted with an alkyl group, a halogen, and a nitro group, and 
 m represents an integer selected from 1-8; and 
 wherein the cation polymerizable monomer has a structure represented by formula (IV): 
 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , and m have the same definitions as those for formula (I). 
       
     
     
       2. The cation polymerizable monomer according to  claim 1 , wherein m is selected to be a numeric value of 2 or more; or when m=1, R 1  is substituted by at least one oxetanyl group. 
     
     
       3. The cation polymerizable monomer according to  claim 1 , wherein R 1  represents a C 1 -C 40  linear m-valent alkyl group, a C 1 -C 40  branched m-valent alkyl group, a C 2 -C 10  linear m-valent alkenyl group, a C 2 -C 10  branched m-valent alkenyl group, or a C 6 -C 30  m-valent aryl group, wherein —CH 2 — can be substituted with an oxygen atom, —NH—, or 
       
         
           
           
               
               
           
         
       
       provided that two —O-'s are not directly connected, and wherein one or more hydrogen atoms in these groups can be each independently substituted with an alkyl group, a halogen, or a nitro group. 
     
     
       4. The cation polymerizable monomer according to  claim 1 , wherein R 2  represents a C 1 -C 10  linear alkylene group or a C 1 -C 10  branched alkylene group, wherein —CH 2 — in the main chain can be substituted with an oxygen atom, provided that two —O-'s are not directly connected. 
     
     
       5. The cation polymerizable monomer according to  claim 1 , wherein R 3  represents hydrogen, a C 1 -C 10  linear alkyl group, a C 1 -C 10  branched alkyl group, a C 3 -C 10  cycloalkyl group, a C 4 -C 10  cycloalkylalkyl group, a C 4 -C 10  alkylcycloalkyl group, a C 2 -C 8  alkenyl group, or a phenyl group. 
     
     
       6. The cation polymerizable monomer according to  claim 1 , wherein m is an integer selected from 1-6. 
     
     
       7. The cation polymerizable monomer according to  claim 1 , wherein m is an integer selected from 1-4. 
     
     
       8. The cation polymerizable monomer according to  claim 1 , wherein R 1  is: a C 1 -C 12  linear 1-to-4-valent alkyl group, a C 1 -C 12  branched 1-to-4-valent alkyl group, a C 2 -C 6  linear 1-to-4-valent alkenyl group, a C 2 -C 6  branched 1-to-4-valent alkenyl group, 
       
         
           
           
               
               
           
         
       
       wherein * represents a bond, wherein x is an integer selected from the range of 0 to 6, y is an integer selected from the range of 0 to 6, and z is an integer selected from the range of 0 to 6. 
     
     
       9. The cation polymerizable monomer according to  claim 1 , wherein R 3  represents a C 1 -C 4  linear alkyl group, a C 1 -C 4  branched alkyl group or a C 4 -C 8  cycloalkylalkyl group. 
     
     
       10. A production method of the cation polymerizable monomer represented by formula (IV) of  claim 1 , wherein the production method comprises performing a reaction, under a basic condition at one or more reaction temperatures selected from 25-120° C., between a polyfunctional oxetane-based compound represented by formula (I) and epichlorohydrin to obtain the cation polymerizable monomer, wherein a reaction formula is as follows: